4-(Methyl­sulfan­yl)benzamide oxime

In the title compound, C₈H₁₀N₂O₂S, there are four mol­ecules in the asymmetric unit. Each possesses an intra­molecular N—H...O hydrogen bond, and a network of inter­molecular N—H...O and O—H...N hydrogen-bond inter­actions helps to consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.143
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C26
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.40
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.14
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3C    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N5     -   H5B    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N8     -   H8B    ...          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97.

4-(Methylsulfanyl)benzamide oxime

Crystal data

C8H10N2OS	Z = 8
Mr = 182.24	F(000) = 768
Triclinic, P1	Dx = 1.365 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.221 (2) Å	Cell parameters from 25 reflections
b = 11.882 (2) Å	θ = 10–13°
c = 17.120 (3) Å	µ = 0.32 mm^−1
α = 74.12 (3)°	T = 293 K
β = 72.91 (3)°	Block, colourless
γ = 64.94 (3)°	0.30 × 0.30 × 0.20 mm
V = 1773.4 (6) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	4669 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 26.0°, θmin = 1.3°
ω/2θ scans	h = −11→12
Absorption correction: ψ scan (North et al., 1968)	k = −13→14
Tmin = 0.911, Tmax = 0.939	l = 0→21
7363 measured reflections	3 standard reflections every 200 reflections
6959 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0505P)^2 + 1.1244P] where P = (Fo^2 + 2Fc^2)/3
6959 reflections	(Δ/σ)max < 0.001
437 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.48945 (12)	0.40461 (10)	0.09806 (6)	0.0766 (3)
O1	0.7601 (3)	−0.1447 (2)	0.48180 (14)	0.0555 (6)
H1A	0.7875	−0.1312	0.5176	0.083*
N1	0.5442 (3)	−0.0942 (2)	0.41668 (16)	0.0539 (7)
H1B	0.5662	−0.1564	0.4567	0.065*
H1C	0.4709	−0.0789	0.3953	0.065*
N2	0.7357 (3)	−0.0371 (2)	0.41583 (15)	0.0474 (6)
C1	0.3099 (5)	0.4323 (4)	0.0881 (3)	0.0935 (15)
H1D	0.2841	0.4980	0.0416	0.140*
H1E	0.2403	0.4574	0.1377	0.140*
H1F	0.3082	0.3565	0.0795	0.140*
C2	0.5204 (4)	0.2833 (3)	0.18498 (19)	0.0497 (8)
C3	0.6644 (4)	0.2142 (3)	0.1938 (2)	0.0648 (10)
H3A	0.7404	0.2336	0.1549	0.078*
C4	0.6970 (4)	0.1172 (3)	0.2592 (2)	0.0605 (9)
H4A	0.7949	0.0724	0.2641	0.073*
C5	0.5871 (3)	0.0846 (3)	0.31812 (17)	0.0399 (6)
C6	0.4428 (3)	0.1551 (3)	0.30967 (19)	0.0523 (8)
H6A	0.3669	0.1359	0.3489	0.063*
C7	0.4088 (3)	0.2534 (3)	0.24426 (19)	0.0557 (9)
H7A	0.3108	0.2996	0.2400	0.067*
C8	0.6244 (3)	−0.0211 (3)	0.38759 (17)	0.0402 (6)
S2	−0.02780 (11)	0.38273 (8)	0.09419 (5)	0.0573 (2)
O2	0.2136 (2)	−0.11227 (18)	0.50618 (12)	0.0488 (5)
H2B	0.2230	−0.0902	0.5449	0.073*
N3	0.0830 (3)	−0.1242 (2)	0.40450 (15)	0.0463 (6)
H3B	0.1061	−0.1845	0.4454	0.056*
H3C	0.0366	−0.1283	0.3715	0.056*
N4	0.1889 (3)	−0.0086 (2)	0.43827 (14)	0.0415 (6)
C9	0.0175 (5)	0.3032 (4)	0.0108 (2)	0.0777 (12)
H9A	−0.0055	0.3638	−0.0383	0.116*
H9B	−0.0384	0.2503	0.0241	0.116*
H9C	0.1209	0.2522	0.0012	0.116*
C10	0.0201 (3)	0.2604 (3)	0.17809 (17)	0.0386 (6)
C15	0.0610 (3)	0.1345 (3)	0.17562 (18)	0.0452 (7)
H15A	0.0674	0.1104	0.1269	0.054*
C14	0.0926 (3)	0.0438 (3)	0.24562 (18)	0.0440 (7)
H14A	0.1197	−0.0406	0.2431	0.053*
C13	0.0847 (3)	0.0762 (2)	0.31894 (16)	0.0343 (6)
C12	0.0431 (3)	0.2032 (3)	0.32159 (18)	0.0430 (7)
H12A	0.0364	0.2273	0.3704	0.052*
C11	0.0120 (3)	0.2930 (3)	0.25214 (18)	0.0470 (7)
H11A	−0.0150	0.3773	0.2547	0.056*
C16	0.1196 (3)	−0.0227 (2)	0.39209 (17)	0.0365 (6)
C17	0.4912 (4)	1.0225 (3)	0.1307 (2)	0.0700 (10)
H17A	0.4979	1.0898	0.0854	0.105*
H17B	0.5451	1.0165	0.1700	0.105*
H17C	0.3896	1.0392	0.1572	0.105*
S3	0.56700 (11)	0.87846 (9)	0.09270 (5)	0.0610 (3)
O3	0.4078 (2)	0.37166 (19)	0.49975 (13)	0.0544 (6)
H3D	0.3307	0.3851	0.5347	0.082*
N5	0.6444 (3)	0.3649 (3)	0.39439 (18)	0.0655 (8)
H5A	0.6425	0.3032	0.4346	0.079*
H5B	0.7257	0.3614	0.3596	0.079*
N6	0.3943 (3)	0.4798 (2)	0.43520 (15)	0.0459 (6)
C18	0.5470 (3)	0.7645 (3)	0.18147 (18)	0.0431 (7)
C19	0.6160 (4)	0.6390 (3)	0.1719 (2)	0.0603 (9)
H19A	0.6694	0.6190	0.1200	0.072*
C20	0.6069 (4)	0.5438 (3)	0.2375 (2)	0.0569 (9)
H20A	0.6544	0.4605	0.2294	0.068*
C21	0.5281 (3)	0.5701 (3)	0.31561 (17)	0.0398 (6)
C22	0.4587 (3)	0.6951 (3)	0.32520 (18)	0.0461 (7)
H22A	0.4046	0.7148	0.3771	0.055*
C23	0.4677 (3)	0.7915 (3)	0.25957 (18)	0.0481 (7)
H23A	0.4205	0.8749	0.2678	0.058*
C24	0.5204 (3)	0.4670 (3)	0.38593 (18)	0.0415 (7)
S4	0.03648 (10)	0.89443 (8)	0.09290 (5)	0.0565 (2)
O4	−0.1098 (2)	0.37745 (18)	0.49272 (13)	0.0509 (5)
H4C	−0.1889	0.3916	0.5260	0.076*
N7	−0.1209 (3)	0.4822 (2)	0.42566 (15)	0.0450 (6)
N8	0.1324 (3)	0.3972 (2)	0.41537 (15)	0.0474 (6)
H8A	0.1273	0.3368	0.4560	0.057*
H8B	0.2166	0.4021	0.3904	0.057*
C25	0.2255 (5)	0.8653 (4)	0.0487 (3)	0.0924 (14)
H25A	0.2340	0.9281	0.0005	0.139*
H25B	0.2724	0.7833	0.0331	0.139*
H25C	0.2725	0.8687	0.0886	0.139*
C26	0.0383 (3)	0.7734 (3)	0.17945 (18)	0.0426 (7)
C27	0.1591 (4)	0.6976 (3)	0.2147 (2)	0.0592 (9)
H27A	0.2484	0.7086	0.1923	0.071*
C28	0.1484 (3)	0.6053 (3)	0.2833 (2)	0.0558 (9)
H28A	0.2313	0.5551	0.3061	0.067*
C29	0.0184 (3)	0.5855 (3)	0.31867 (16)	0.0385 (6)
C30	−0.1029 (3)	0.6627 (3)	0.2829 (2)	0.0592 (9)
H30A	−0.1924	0.6520	0.3052	0.071*
C31	−0.0925 (4)	0.7543 (3)	0.2151 (2)	0.0636 (10)
H31A	−0.1755	0.8050	0.1925	0.076*
C32	0.0083 (3)	0.4844 (2)	0.39080 (16)	0.0370 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0731 (6)	0.0820 (7)	0.0659 (6)	−0.0406 (6)	−0.0282 (5)	0.0351 (5)
O1	0.0649 (15)	0.0516 (13)	0.0517 (13)	−0.0275 (11)	−0.0281 (11)	0.0152 (10)
N1	0.0568 (17)	0.0532 (16)	0.0593 (17)	−0.0336 (14)	−0.0240 (13)	0.0134 (13)
N2	0.0508 (15)	0.0481 (15)	0.0447 (14)	−0.0257 (12)	−0.0215 (12)	0.0146 (11)
C1	0.089 (3)	0.105 (3)	0.078 (3)	−0.042 (3)	−0.044 (2)	0.034 (3)
C2	0.057 (2)	0.0484 (18)	0.0448 (17)	−0.0251 (16)	−0.0165 (15)	0.0051 (14)
C3	0.050 (2)	0.082 (3)	0.057 (2)	−0.0386 (19)	−0.0140 (16)	0.0231 (19)
C4	0.0443 (18)	0.079 (2)	0.055 (2)	−0.0322 (18)	−0.0182 (15)	0.0184 (18)
C5	0.0437 (16)	0.0431 (16)	0.0336 (15)	−0.0204 (13)	−0.0089 (12)	0.0004 (12)
C6	0.0409 (17)	0.060 (2)	0.0429 (17)	−0.0195 (15)	−0.0017 (13)	0.0042 (15)
C7	0.0406 (17)	0.061 (2)	0.0463 (18)	−0.0120 (15)	−0.0050 (14)	0.0050 (15)
C8	0.0410 (16)	0.0402 (16)	0.0373 (15)	−0.0171 (13)	−0.0058 (12)	−0.0026 (12)
S2	0.0785 (6)	0.0418 (4)	0.0480 (5)	−0.0192 (4)	−0.0225 (4)	0.0030 (4)
O2	0.0550 (13)	0.0427 (11)	0.0446 (12)	−0.0181 (10)	−0.0188 (10)	0.0077 (9)
N3	0.0545 (15)	0.0363 (13)	0.0515 (15)	−0.0226 (12)	−0.0163 (12)	0.0023 (11)
N4	0.0440 (14)	0.0398 (13)	0.0383 (13)	−0.0183 (11)	−0.0112 (11)	0.0044 (10)
C9	0.113 (3)	0.067 (2)	0.042 (2)	−0.026 (2)	−0.018 (2)	−0.0013 (18)
C10	0.0373 (15)	0.0379 (15)	0.0412 (16)	−0.0156 (12)	−0.0092 (12)	−0.0038 (12)
C15	0.0598 (19)	0.0403 (16)	0.0374 (16)	−0.0193 (14)	−0.0097 (14)	−0.0092 (13)
C14	0.0534 (18)	0.0319 (15)	0.0477 (17)	−0.0172 (13)	−0.0091 (14)	−0.0075 (13)
C13	0.0295 (14)	0.0365 (14)	0.0352 (14)	−0.0126 (11)	−0.0076 (11)	−0.0019 (11)
C12	0.0516 (18)	0.0405 (16)	0.0422 (16)	−0.0182 (14)	−0.0142 (13)	−0.0087 (13)
C11	0.0576 (19)	0.0339 (15)	0.0511 (18)	−0.0161 (14)	−0.0182 (15)	−0.0034 (13)
C16	0.0286 (14)	0.0367 (15)	0.0383 (15)	−0.0108 (12)	−0.0007 (11)	−0.0062 (12)
C17	0.088 (3)	0.055 (2)	0.063 (2)	−0.036 (2)	−0.009 (2)	0.0031 (18)
S3	0.0772 (6)	0.0578 (5)	0.0402 (5)	−0.0298 (5)	−0.0063 (4)	0.0047 (4)
O3	0.0513 (13)	0.0468 (12)	0.0514 (13)	−0.0208 (10)	−0.0101 (10)	0.0163 (10)
N5	0.0421 (16)	0.0535 (17)	0.0665 (19)	−0.0060 (13)	0.0004 (13)	0.0105 (14)
N6	0.0411 (14)	0.0419 (14)	0.0448 (14)	−0.0172 (11)	−0.0076 (11)	0.0091 (11)
C18	0.0420 (16)	0.0465 (17)	0.0389 (16)	−0.0190 (14)	−0.0070 (13)	−0.0019 (13)
C19	0.074 (2)	0.056 (2)	0.0380 (17)	−0.0231 (18)	0.0056 (16)	−0.0098 (15)
C20	0.069 (2)	0.0415 (17)	0.0497 (19)	−0.0175 (16)	−0.0008 (16)	−0.0091 (15)
C21	0.0322 (15)	0.0409 (16)	0.0392 (16)	−0.0129 (12)	−0.0063 (12)	0.0015 (12)
C22	0.0446 (17)	0.0434 (17)	0.0381 (16)	−0.0120 (14)	−0.0008 (13)	−0.0038 (13)
C23	0.0513 (19)	0.0382 (16)	0.0415 (17)	−0.0104 (14)	−0.0050 (14)	−0.0018 (13)
C24	0.0365 (16)	0.0381 (15)	0.0447 (17)	−0.0114 (13)	−0.0109 (13)	−0.0006 (13)
S4	0.0745 (6)	0.0546 (5)	0.0458 (5)	−0.0375 (5)	−0.0159 (4)	0.0090 (4)
O4	0.0534 (13)	0.0376 (11)	0.0490 (13)	−0.0200 (10)	−0.0021 (10)	0.0078 (9)
N7	0.0455 (15)	0.0386 (13)	0.0442 (14)	−0.0191 (11)	−0.0060 (11)	0.0052 (11)
N8	0.0382 (14)	0.0422 (14)	0.0521 (15)	−0.0129 (11)	−0.0094 (11)	0.0035 (12)
C25	0.086 (3)	0.103 (3)	0.071 (3)	−0.051 (3)	0.002 (2)	0.018 (2)
C26	0.0531 (18)	0.0411 (16)	0.0389 (16)	−0.0251 (14)	−0.0106 (13)	−0.0014 (13)
C27	0.0496 (19)	0.068 (2)	0.063 (2)	−0.0357 (18)	−0.0144 (16)	0.0109 (17)
C28	0.0401 (17)	0.058 (2)	0.063 (2)	−0.0224 (15)	−0.0174 (15)	0.0133 (16)
C29	0.0423 (16)	0.0383 (15)	0.0354 (15)	−0.0174 (13)	−0.0077 (12)	−0.0034 (12)
C30	0.0371 (17)	0.068 (2)	0.061 (2)	−0.0250 (16)	−0.0151 (15)	0.0200 (17)
C31	0.0485 (19)	0.061 (2)	0.067 (2)	−0.0216 (17)	−0.0201 (17)	0.0232 (18)
C32	0.0406 (16)	0.0340 (14)	0.0358 (15)	−0.0145 (12)	−0.0049 (12)	−0.0071 (12)

Geometric parameters (Å, º)

S1—C2	1.763 (3)	C17—S3	1.772 (4)
S1—C1	1.774 (4)	C17—H17A	0.9600
O1—N2	1.442 (3)	C17—H17B	0.9600
O1—H1A	0.8200	C17—H17C	0.9600
N1—C8	1.342 (3)	S3—C18	1.764 (3)
N1—H1B	0.8600	O3—N6	1.433 (3)
N1—H1C	0.8600	O3—H3D	0.8200
N2—C8	1.286 (4)	N5—C24	1.345 (4)
C1—H1D	0.9600	N5—H5A	0.8600
C1—H1E	0.9600	N5—H5B	0.8600
C1—H1F	0.9600	N6—C24	1.288 (4)
C2—C3	1.379 (4)	C18—C19	1.386 (4)
C2—C7	1.387 (4)	C18—C23	1.388 (4)
C3—C4	1.371 (4)	C19—C20	1.371 (4)
C3—H3A	0.9300	C19—H19A	0.9300
C4—C5	1.385 (4)	C20—C21	1.385 (4)
C4—H4A	0.9300	C20—H20A	0.9300
C5—C6	1.382 (4)	C21—C22	1.381 (4)
C5—C8	1.477 (4)	C21—C24	1.475 (4)
C6—C7	1.381 (4)	C22—C23	1.381 (4)
C6—H6A	0.9300	C22—H22A	0.9300
C7—H7A	0.9300	C23—H23A	0.9300
S2—C10	1.756 (3)	S4—C26	1.758 (3)
S2—C9	1.768 (4)	S4—C25	1.773 (4)
O2—N4	1.435 (3)	O4—N7	1.434 (3)
O2—H2B	0.8200	O4—H4C	0.8200
N3—C16	1.355 (3)	N7—C32	1.288 (3)
N3—H3B	0.8600	N8—C32	1.350 (3)
N3—H3C	0.8600	N8—H8A	0.8600
N4—C16	1.287 (3)	N8—H8B	0.8600
C9—H9A	0.9600	C25—H25A	0.9600
C9—H9B	0.9600	C25—H25B	0.9600
C9—H9C	0.9600	C25—H25C	0.9600
C10—C15	1.382 (4)	C26—C27	1.378 (4)
C10—C11	1.394 (4)	C26—C31	1.383 (4)
C15—C14	1.388 (4)	C27—C28	1.384 (4)
C15—H15A	0.9300	C27—H27A	0.9300
C14—C13	1.382 (4)	C28—C29	1.379 (4)
C14—H14A	0.9300	C28—H28A	0.9300
C13—C12	1.394 (4)	C29—C30	1.389 (4)
C13—C16	1.476 (4)	C29—C32	1.482 (4)
C12—C11	1.376 (4)	C30—C31	1.370 (4)
C12—H12A	0.9300	C30—H30A	0.9300
C11—H11A	0.9300	C31—H31A	0.9300
C2—S1—C1	104.10 (17)	S3—C17—H17A	109.5
N2—O1—H1A	109.5	S3—C17—H17B	109.5
C8—N1—H1B	120.0	H17A—C17—H17B	109.5
C8—N1—H1C	120.0	S3—C17—H17C	109.5
H1B—N1—H1C	120.0	H17A—C17—H17C	109.5
C8—N2—O1	109.6 (2)	H17B—C17—H17C	109.5
S1—C1—H1D	109.5	C18—S3—C17	104.62 (16)
S1—C1—H1E	109.5	N6—O3—H3D	109.5
H1D—C1—H1E	109.5	C24—N5—H5A	120.0
S1—C1—H1F	109.5	C24—N5—H5B	120.0
H1D—C1—H1F	109.5	H5A—N5—H5B	120.0
H1E—C1—H1F	109.5	C24—N6—O3	110.1 (2)
C3—C2—C7	118.5 (3)	C19—C18—C23	118.1 (3)
C3—C2—S1	117.7 (2)	C19—C18—S3	117.2 (2)
C7—C2—S1	123.8 (2)	C23—C18—S3	124.8 (2)
C4—C3—C2	120.9 (3)	C20—C19—C18	121.3 (3)
C4—C3—H3A	119.5	C20—C19—H19A	119.4
C2—C3—H3A	119.5	C18—C19—H19A	119.4
C3—C4—C5	121.3 (3)	C19—C20—C21	121.0 (3)
C3—C4—H4A	119.3	C19—C20—H20A	119.5
C5—C4—H4A	119.3	C21—C20—H20A	119.5
C6—C5—C4	117.6 (3)	C22—C21—C20	117.8 (3)
C6—C5—C8	121.8 (3)	C22—C21—C24	121.6 (3)
C4—C5—C8	120.6 (3)	C20—C21—C24	120.6 (3)
C5—C6—C7	121.5 (3)	C21—C22—C23	121.6 (3)
C5—C6—H6A	119.2	C21—C22—H22A	119.2
C7—C6—H6A	119.2	C23—C22—H22A	119.2
C6—C7—C2	120.1 (3)	C22—C23—C18	120.2 (3)
C6—C7—H7A	119.9	C22—C23—H23A	119.9
C2—C7—H7A	119.9	C18—C23—H23A	119.9
N2—C8—N1	124.2 (3)	N6—C24—N5	123.9 (3)
N2—C8—C5	116.1 (2)	N6—C24—C21	117.8 (2)
N1—C8—C5	119.7 (3)	N5—C24—C21	118.3 (3)
C10—S2—C9	103.88 (15)	C26—S4—C25	104.34 (18)
N4—O2—H2B	109.5	N7—O4—H4C	109.5
C16—N3—H3B	120.0	C32—N7—O4	109.8 (2)
C16—N3—H3C	120.0	C32—N8—H8A	120.0
H3B—N3—H3C	120.0	C32—N8—H8B	120.0
C16—N4—O2	109.9 (2)	H8A—N8—H8B	120.0
S2—C9—H9A	109.5	S4—C25—H25A	109.5
S2—C9—H9B	109.5	S4—C25—H25B	109.5
H9A—C9—H9B	109.5	H25A—C25—H25B	109.5
S2—C9—H9C	109.5	S4—C25—H25C	109.5
H9A—C9—H9C	109.5	H25A—C25—H25C	109.5
H9B—C9—H9C	109.5	H25B—C25—H25C	109.5
C15—C10—C11	118.3 (3)	C27—C26—C31	117.9 (3)
C15—C10—S2	123.8 (2)	C27—C26—S4	125.0 (2)
C11—C10—S2	117.8 (2)	C31—C26—S4	117.1 (2)
C10—C15—C14	120.2 (3)	C26—C27—C28	120.4 (3)
C10—C15—H15A	119.9	C26—C27—H27A	119.8
C14—C15—H15A	119.9	C28—C27—H27A	119.8
C13—C14—C15	121.4 (3)	C29—C28—C27	121.9 (3)
C13—C14—H14A	119.3	C29—C28—H28A	119.1
C15—C14—H14A	119.3	C27—C28—H28A	119.1
C14—C13—C12	118.4 (2)	C28—C29—C30	117.3 (3)
C14—C13—C16	120.0 (2)	C28—C29—C32	121.8 (3)
C12—C13—C16	121.6 (3)	C30—C29—C32	121.0 (3)
C11—C12—C13	120.1 (3)	C31—C30—C29	120.9 (3)
C11—C12—H12A	119.9	C31—C30—H30A	119.6
C13—C12—H12A	119.9	C29—C30—H30A	119.6
C12—C11—C10	121.5 (3)	C30—C31—C26	121.7 (3)
C12—C11—H11A	119.3	C30—C31—H31A	119.1
C10—C11—H11A	119.3	C26—C31—H31A	119.1
N4—C16—N3	124.2 (3)	N7—C32—N8	123.0 (3)
N4—C16—C13	117.1 (2)	N7—C32—C29	117.3 (2)
N3—C16—C13	118.6 (2)	N8—C32—C29	119.7 (2)
C1—S1—C2—C3	160.4 (3)	C17—S3—C18—C19	−171.2 (3)
C1—S1—C2—C7	−19.2 (4)	C17—S3—C18—C23	8.7 (3)
C7—C2—C3—C4	0.6 (6)	C23—C18—C19—C20	−0.2 (5)
S1—C2—C3—C4	−179.0 (3)	S3—C18—C19—C20	179.8 (3)
C2—C3—C4—C5	0.5 (6)	C18—C19—C20—C21	0.1 (6)
C3—C4—C5—C6	−1.3 (5)	C19—C20—C21—C22	0.2 (5)
C3—C4—C5—C8	179.3 (3)	C19—C20—C21—C24	−179.3 (3)
C4—C5—C6—C7	1.0 (5)	C20—C21—C22—C23	−0.4 (5)
C8—C5—C6—C7	−179.6 (3)	C24—C21—C22—C23	179.0 (3)
C5—C6—C7—C2	0.2 (5)	C21—C22—C23—C18	0.4 (5)
C3—C2—C7—C6	−1.0 (5)	C19—C18—C23—C22	−0.1 (5)
S1—C2—C7—C6	178.7 (3)	S3—C18—C23—C22	179.9 (2)
O1—N2—C8—N1	0.5 (4)	O3—N6—C24—N5	1.1 (4)
O1—N2—C8—C5	−178.8 (2)	O3—N6—C24—C21	−179.7 (2)
C6—C5—C8—N2	−145.1 (3)	C22—C21—C24—N6	43.8 (4)
C4—C5—C8—N2	34.3 (4)	C20—C21—C24—N6	−136.8 (3)
C6—C5—C8—N1	35.6 (4)	C22—C21—C24—N5	−136.9 (3)
C4—C5—C8—N1	−145.0 (3)	C20—C21—C24—N5	42.5 (4)
C9—S2—C10—C15	−8.7 (3)	C25—S4—C26—C27	15.4 (4)
C9—S2—C10—C11	173.3 (3)	C25—S4—C26—C31	−165.4 (3)
C11—C10—C15—C14	0.1 (4)	C31—C26—C27—C28	0.4 (5)
S2—C10—C15—C14	−177.9 (2)	S4—C26—C27—C28	179.6 (3)
C10—C15—C14—C13	−0.2 (5)	C26—C27—C28—C29	0.0 (6)
C15—C14—C13—C12	0.4 (4)	C27—C28—C29—C30	−0.2 (5)
C15—C14—C13—C16	−179.7 (3)	C27—C28—C29—C32	178.4 (3)
C14—C13—C12—C11	−0.5 (4)	C28—C29—C30—C31	0.1 (5)
C16—C13—C12—C11	179.7 (3)	C32—C29—C30—C31	−178.6 (3)
C13—C12—C11—C10	0.4 (5)	C29—C30—C31—C26	0.3 (6)
C15—C10—C11—C12	−0.2 (4)	C27—C26—C31—C30	−0.6 (5)
S2—C10—C11—C12	177.9 (2)	S4—C26—C31—C30	−179.8 (3)
O2—N4—C16—N3	−3.0 (4)	O4—N7—C32—N8	1.1 (4)
O2—N4—C16—C13	179.9 (2)	O4—N7—C32—C29	178.8 (2)
C14—C13—C16—N4	142.5 (3)	C28—C29—C32—N7	172.1 (3)
C12—C13—C16—N4	−37.6 (4)	C30—C29—C32—N7	−9.2 (4)
C14—C13—C16—N3	−34.7 (4)	C28—C29—C32—N8	−10.1 (4)
C12—C13—C16—N3	145.1 (3)	C30—C29—C32—N8	168.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1	0.86	2.21	2.535 (3)	102
N3—H3B···O2	0.86	2.23	2.548 (3)	102
N5—H5A···O3	0.86	2.22	2.542 (3)	102
N8—H8A···O4	0.86	2.19	2.517 (3)	103
N1—H1C···N4	0.86	2.57	3.263 (4)	139
N1—H1B···O3^i	0.86	2.38	3.101 (3)	142
N3—H3B···O4^ii	0.86	2.24	2.986 (3)	146
N5—H5A···O2^i	0.86	2.27	2.997 (3)	143
N8—H8A···O1^i	0.86	2.20	2.960 (3)	148
O1—H1A···N4^i	0.82	2.13	2.838 (3)	145
O2—H2B···N2^i	0.82	2.04	2.772 (3)	148
O3—H3D···N7^iii	0.82	2.10	2.818 (3)	146
O4—H4C···N6^iii	0.82	2.05	2.777 (3)	148

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y, −z+1; (iii) −x, −y+1, −z+1.